Financial Planning For Wealth Events

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Major financial events don’t have to be stressful. We help you make the most of your momentum, with clarity, calm, and strategy.

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Financial Planning For Wealth Events
Financial Planning For Wealth Events

Big transitions bring big questions. You might be selling your company, facing a liquidity event, changing your marital status or stepping into sudden wealth and you know the decisions you make now will shape your future for years. This is where we shine.

At Chesapeake, we specialize in moments like these. Not because we have a crystal ball—but because we’ve helped dozens of smart, successful people like you navigate pivotal change with confidence and precision.

We won’t give you a cookie cutter plan or throw jargon your way. We’ll help you slow down, zoom out, and put every dollar to work for the life you actually want. Let’s make your next move the right one.

Wealth Events Case Study

Finding Clarity and the Confidence to Make A Change

When Sally’s uncle, Charlie, passed away, she and her husband, Dave, faced more than grief. Along with the memories came a meaningful inheritance that she wanted to handle wisely. Unsure where to start, she called Jeff. Her uncle had often mentioned how much he trusted him, and she wanted guidance on what to do next.

From their first conversation, Jeff’s approach felt different. He did not begin with charts or returns. He asked about Charlie, who he was, what mattered to him, and how Sally wanted to carry forward his legacy. As they talked, Sally felt a sense of calm she had not experienced in years of financial conversations. She realized she was finally being listened to.

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Chesapeake Financial Planners place picture
5.0
Based on 13 reviews
Thomas Cowley profile picture
Thomas Cowley
7 days ago
Mark and Jeff have handled my finances for over a decade. They have been great stewards for my investments which have grown substantially. They listen to my goals and give me recommendations and options to carry them out. I highly recommend them.
Jane Towery profile picture
Jane Towery
3 months ago
I have been extremely pleased with Mark’s services over the last 15 years and would very highly recommend. Mark has taken the time to get to know my needs, interests, long and short term goals. We evaluate my portfolio yearly for any adjustments, reevaluation, or study trends. Mark objectively presents the pros and cons of options, answers questions, and leaves the final decision to me. I have never felt pressured and always appreciate how understood and listened to I have felt. More recently I have had some opportunity to work with Jeff as well. Mark and Jeff present a unified team who want to make your investments work for your needs.
Joyce Ducksworth profile picture
Joyce Ducksworth
5 months ago
I have had the pleasure of entrusting my finances with Jeff and Mark for many years. Their expertise and advice are invaluable. My portfolio has grown significantly and has allowed me to retire comfortably with tremendous financial security. Mark is always available to answer my questions and provide solutions. I highly recommend Chesapeake Financial Planners.
stephen kinsley profile picture
stephen kinsley
5 months ago
Mark and Jeff have been my retirement advisors since 2011 and I could not be happier with them. They are knowledgeable and easy to talk with. They respond quickly to any questions and clearly explain all my options. I have been retired for 5 years and am fully confident that my financial future will continue to improve as it has so far with them. I would recommend them to anyone, and I only wish that I had met them sooner.
Bob Burris profile picture
Bob Burris
6 months ago
I have been working with Mark and Jeff for 10+ years. I recently asked for a review of my financial plan and was provided outstanding feedback that provided me a much better solution.
Kim Wright profile picture
Kim Wright
7 months ago
I am delighted with LPL. They've stayed with me for years and Jeff Judge has been exceptionally helpful. I've gotten good advice. He's managed my assets professionally and has always been available answer my questions. He helped me consolidate several accounts into one manageable asset. He took the guesswork out of what could have been a complicated process. I trust him to be there and guide me through issues in which I have no expertise. But he does this all the time and has proven to be trustworthy. I do recommend Mr. Judge. You will not be disappointed.
Sharon Lewis profile picture
Sharon Lewis
7 months ago
My husband and I met Mark and Jeff in 2014 when my husband left his job after 23 years. We met with Mark and Jeff to decide where to invest his retirement money. Before that decision was made, they took their time to understand our entire financial picture and based on that they gave us several options on where we could invest. They were very easy to talk with and made the conversation easy to understand. They are easy to get in touch with if you have questions and provide answers quickly. When it came time for me to retire, I also rolled my retirement investments into accounts managed by Mark and Jeff. We have also setup our estate planning as well as long term health planning based on advice we have had in review meetings in the years following our initial meeting. We have even referred our daughter and son in law to them. Highly satisfied with the investment service and customer service.
Andrew Benner profile picture
Andrew Benner
7 months ago
I check in with Mark a couple times a year and he always helps me keep my money that he manages growing. He also helps us with general advise regarding the type of places our 401k money should be (growth vs value, etc)
Mark Gray profile picture
Mark Gray
9 months ago
Jeff has been helping me since 2014 with life insurance and retirement investment products. After a bad experience with a big insurance company, I found Mark and I’ve been working with him ever since. I’m successfully retired now and will begin drawing on my investments this year. I highly recommend Chesapeake Financial Planners for your retirement planning. – Mark G.
David Carrington profile picture
David Carrington
10 months ago
Jeff has been my financial advisor/ planner for several years. He has always guided me in the right direction and I have seen my retirement account continuously moving in the right direction. During the current uncertainty of the financial world right now Jeff has given me peace of mind that I continue to be in a safe and secure position with my finances. Jeff is very professional and quick to respond to my emails. As I approach my retirement years it is comforting to know my finances will be there when I need them.
Matt Hurson profile picture
Matt Hurson
11 months ago
I have been working with Jeff Judge and Chesapeake Financial Planners for about 3 years. Jeff has provided timely and well considered advice and acted promptly when I've needed access and changes to my portfolio. Highly recommend their services.
John Komoroski profile picture
John Komoroski
12 months ago
We have worked with Jeff at Chesapeake Financial Planners for over 10 years. Throughout that time he has provided valuable investment and retirement information. Our investments have navigated this turbulent market far better than expected. Thank you Jeff.
Charles Gaither profile picture
Charles Gaither
12 months ago
I've been working with Chesapeake Financial Planners for a little over six years, and it's been an outstanding experience. They're knowledgeable, responsive, and consistently provide clear, personalized advice that aligns with my financial goals. Their long-term commitment and reliability have given me real peace of mind.

Wealth Events

Switching Jobs

You’ve Changed Jobs. Let’s Make Sure Your Money Keeps Up.

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Inheritence

Sudden Wealth, Complex Emotions. Smart Moves Start Here.

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Marriage

Financial partnership for your biggest partnership yet.

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Divorce

This Isn’t Starting Over. It’s Taking Control.

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Sale of Business

Selling Was Just Step One.

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Stock Options

You worked hard for this moment. Don’t let taxes or timing steal it.

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Lump Sum

You’ve Got One Shot to Get This Right. Let’s Make Sure You Do.

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Windfall

Sudden Wealth? Let’s Turn This Moment into a Life Well Lived.

Learn More →

Frequently Asked Questions

When life changes suddenly, the right financial response is to stop, assess, and rebuild your plan around your new reality before making any major moves. That means reviewing your cash flow, revisiting your goals, and checking insurance and estate documents before acting on anything.

Six steps to take in order:

1. Pause and take stock: Identify what changed, what's urgent, and what can wait before touching a single account.
2. Update your cash flow plan: Income, expenses, or priorities likely shifted. Rebuild the budget to fit the new reality.
3. Revisit your goals and timeline: A new path may call for a new strategy, including your investment plan, retirement target, or debt repayment.
4. Review insurance and legal documents: Life changes affect who and what needs protection.
5. Understand the tax impact: Layoffs, lump sums, and sudden events often bring tax surprises. Plan ahead.
6. Rebuild your cash reserve: Emergency funds and flexible investments reduce exposure to the next disruption.

You avoid windfall mistakes by doing one thing first: parking the money somewhere safe and making no decisions for at least 30 days. The most expensive mistakes happen in the first weeks, not the first years.

Six mistakes to avoid and how:

1. Acting too fast: Delay every major decision. Put the funds in a high-yield savings account while you build a plan.
2. Lifestyle creep: Set a clear, bounded amount for lifestyle upgrades. Don't let spending expand to fill the balance.
3. Skipping the financial foundation: Pay off high-interest debt, shore up your emergency reserve, and review insurance before investing anything.
4. Ignoring taxes: Depending on the source, windfalls carry real tax consequences. Coordinate with your CPA before gifting or investing.
5. No goal alignment: Know what this money is supposed to do for you before it does anything else.
6. Chasing headlines: Build a disciplined investment plan, not one based on what's trending.

You address financial risk during a major life transition by stabilizing cash flow first, pausing large financial decisions, and reviewing your insurance and estate documents before making any longer-term moves. Protect the present before you plan the future.

Six steps to take when a transition hits:

1. Stabilize cash flow: Confirm you have enough liquidity for immediate needs. Don't touch investments out of fear.
2. Pause large decisions: Unless truly urgent, hold off on major purchases, withdrawals, or investment changes until you've had time to think.
3. Review insurance and legal documents: Health, life, disability, and property coverage may need updating. Check beneficiary designations too.
4. Organize accounts: Consolidate where it makes sense and clarify what's in your control.
5. Adjust your budget: Temporary spending shifts can reduce pressure while you adapt to the change.
6. Rebuild with intention: Once you're stable, update your plan to reflect your new timeline, priorities, and goals.

You should review your investments after a major life event, but not necessarily change them immediately. Whether a rebalance is warranted depends on whether your goals, timeline, income, or risk tolerance actually changed.

How to think through it:

1. Pause before reacting: Decisions made under stress or excitement tend to be the ones you regret. Stabilize cash flow first.
2. Reassess goals and timeline: Did the event shift your retirement target, a major purchase, or your income expectations? If yes, your portfolio may need to reflect that.
3. Review risk tolerance and capacity: You may feel differently about market volatilityThe degree to which investment prices fluctuate over a period of time. Higher volatility means larger and more frequent price swings — which creates anxiety for many investors but also opportunity for those who stay disciplined and maintain a long-term perspective. now. Align your allocation with both your comfort level and your actual financial situation.
4. Account for new cash flow: If income or expenses changed, your investment contributions and liquidity needs may need to change too.
5. Coordinate with tax and estate planning: Windfalls, inheritances, and family changes can create repositioning opportunities that reduce long-term tax costs.

The smartest way to handle inheritance money is to pause before spending, understand exactly what you've inherited and its tax implications, and build a plan that reflects your actual goals before making any moves. Speed is the enemy here.

Six steps that matter most:

1. Wait before deciding: Inheritance often follows loss. Give yourself space before making permanent financial decisions.
2. Identify what you received: Cash, brokerage accounts, IRAs, real estate, and business interests each carry different rules and timelines. Know what you have.
3. Plan for taxes: Most inheritances aren't taxed directly, but inherited IRAs and appreciated assets can trigger taxes if handled incorrectly.
4. Align with your goals: Whether you want to pay off debt, invest, support family, or give, build a plan that reflects your values, not just your balance.
5. Update your own estate plan: An inheritance is the right time to review your beneficiary designations, will, and insurance.
6. Watch for lifestyle inflationThe tendency to increase spending as income rises, making it hard to build wealth even as your salary grows. Getting ahead of lifestyle inflation — by saving raises before adjusting your lifestyle — is one of the most effective ways to accelerate wealth accumulation over your career.: Sudden wealth disappears fastest when spending expands to match the balance. Set a clear budget for discretionary use.

A windfall stays on track when you slow down, establish a plan before spending, and treat taxes and lifestyle inflation as the two most common ways sudden wealth disappears. Most windfalls that derail finances do so in the first 18 months, not over decades.

Six ways to protect what you received:

1. Pause before any major decisions: Park the funds in a high-yield savings account and give yourself 60 to 90 days to think clearly.
2. Separate emotion from action: Windfalls often follow emotionally significant events. Take time before making permanent moves.
3. Define what the money must do: Retirement acceleration, debt payoff, legacy, career change? Name the purpose before building the plan.
4. Manage taxes proactively: Many windfalls carry tax consequences that aren't obvious upfront. Coordinate with your CPA early.
5. Set clear limits on lifestyle changes: Enjoy some of it intentionally. Don't let spending expand permanently to match the balance.
6. Align with your longer-term goals: A windfall can accelerate what you already wanted, early retirement, career freedom, generational giving, if it's handled with a plan.

When you suddenly receive a large sum of money, the smartest first step is to park it in a high-yield savings account and make no major spending or investment decisions for at least 30 days. The plan comes before the purchase.

Six things to do with a large cash influx:

1. Place it safely: A high-yield savings or short-term cash account gives you access and time to think clearly.
2. Clarify its purpose: Is this money for early retirement, a home, debt payoff, or family? Name the goal before you direct a dollar.
3. Build a spending and investing strategy: Prioritize in order: debt, emergency reserve, long-term investment, and then short-term goals.
4. Address the tax consequences: If the source was a taxable event, such as a business sale or stock vesting, coordinate with your CPA now rather than at tax time.
5. Review estate and insurance documents: New wealth changes what needs protection and who should be named in your documents.
6. Spend intentionally, not reactively: A large sum can change your circumstances without changing your values. Decide what it's for, then act.

The first financial step after receiving unexpected money is to move it into a high-yield savings account and make no other decisions for at least 30 days. Pausing is not inaction; it's the most protective move you can make.

Four things to do right away:

1. Place the funds safely: A high-yield savings or short-term cash account keeps the money accessible while you take time to plan.
2. Resist acting immediately: Whether you feel excited, anxious, or overwhelmed, reactive decisions tend to be the ones people regret most.
3. Define the money's purpose: What do you need it to do for you, both now and over the next five to ten years? Clarity here shapes every decision that follows.
4. Check for tax consequences: Before gifting, investing, or paying down debt, confirm how the windfall is taxed. Coordinate with your CPA before making moves.

Hire a financial planner after a life-changing event as soon as the dust starts to settle, and before any major financial decisions are made. The earlier you get structured guidance, the more options you have.

Signs it's time to reach out:

- You've received unexpected money and want to use it thoughtfully rather than impulsively.
- You're facing new decisions around assets, employment, housing, or family structure and aren't sure of the right sequence.
- You don't yet know how the event affects your longer-term goals.
- You want a clear-headed thinking partner during an emotionally charged or high-stakes moment.
- You're concerned about making a mistake that would be hard to reverse.

Yes, a financial planner is most valuable during a major life transition. Retirement, job changes, inheritance, divorce, business exits, and loss all create financial decisions that are hard to make clearly under stress. A planner brings structure when circumstances are disorganized and stakes are high.

Five ways a planner helps during a transition:

1. Slowing you down: A good planner helps you avoid rushed decisions that create lasting setbacks.
2. Organizing complexity: Consolidating accounts, updating beneficiariesThe people or entities designated to receive your assets when you die — through retirement accounts, life insurance policies, or trusts. Keeping beneficiary designations current is one of the simplest but most overlooked parts of estate planning, and outdated designations can completely override what your will says., clarifying priorities, these are tasks that feel overwhelming alone and go faster with a partner.
3. Rebuilding the plan: What worked before may not fit now. Your cash flow, investments, and goals likely need realignment.
4. Reviewing protection: Insurance, estate plans, and risk management often need a fresh review after any significant change.
5. Providing steady guidance: Major transitions are emotional. A planner who knows your full picture can help you act on facts rather than feelings.

The most common financial mistakes during major life changes are acting too quickly on big decisions, ignoring the tax consequences of new wealth, letting lifestyle spending expand to match a windfall, and failing to update insurance and estate documents after a family change. Most of these are avoidable with a plan and a pause.

Six mistakes to watch for:

1. Moving too fast: Selling assets, relocating, or quitting a job before you have a clear plan often leads to decisions you can't undo.
2. Missing the tax bill: Inheritances, business sales, and equity events can trigger surprise tax obligations. Coordinate with your CPA before you spend anything.
3. Lifestyle inflation after a windfall: Without a strategy, spending tends to expand permanently. Set clear boundaries for discretionary use.
4. Outdated insurance and estate documents: Marriage, divorce, new children, or the death of a spouse all require updated beneficiaries, wills, and coverage.
5. Not adjusting the investment plan: Your old allocation may not match your new income, risk tolerance, or time horizon.
6. Handling it alone: Transitions are emotionally loaded. A financial planner helps you make grounded choices when pressure is highest.

*Advisors are only obligated to apply the fiduciary standard in advisory relationships. They are not legally obligated to apply the fiduciary standard when working in Brokerage only relationships

**Mark Rossbach is the only advisor who has attained the RICP and CPA Designations and Jeff Judge is the only advisor who has attained the CFP, ChFC and CLU Designations

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